What Windows logs about USBAll removable storage devices plugged into any Windows based computer are recorded (including the serial number of the device) along with the date/time it was connected and for how long. Any device appearing in the system log for the first time at 02:00 on a Sunday, several days before a person resigned, requires explanation.
Cloud storage and webmailRegardless of which cloud storage service the employee uses (OneDrive, Dropbox, Google Drive or even accessing their webmail through a browser), traces remain on the machine. This includes synchronised database entries, cached access tokens, web browsing histories and partially completed file uploads. Logging off and cleaning up afterwards will not remove most of this information.
Wiping tools and bulk deletionRemoving evidence usually creates much more of it. At minimum, you will be left with the name of the tool used, the date/time it was executed and, ultimately, anything that the tool was unable to delete, which is usually what settles matters.
Sequence is the evidenceEach of these items individually likely has an innocent explanation readily available. However, if viewed collectively while tracking the timing of events (i.e., files gathered, memory stick inserted, upload completed, wiping performed), it is less likely to appear as mere coincidence.